Go With The Flow: Cowork Deep Dive - Skills, Guardrails, and Avoiding Disaster

Jan 30, 2026

Danny and Ritu dive deep into Anthropic's new Cowork feature in Claude Desktop - the good, the bad, and the ugly. Ritu shares a cautionary tale about file deletion gone wrong, while Danny demonstrates his custom skills pack that protects users from common pitfalls.

What You'll Learn:

• What Cowork is and how it differs from Claude Code and Claude Desktop
• Why the rm -rf command can permanently delete your files (and how to prevent it)
• How to set up deny lists in your Claude settings to protect critical files
• The power of skills and bootstrap files for consistent, reliable outputs
• Decision panels: letting Claude guide you through complex choices
• Cascade skills: research to article to slides in one automated flow

Key Timestamps:

• 00:00 - Introduction to Cowork
• 02:13 - Ritu's file deletion disaster story
• 08:37 - Understanding rm vs rm -rf commands
• 10:01 - Setting up deny lists for protection
• 16:00 - Evolution from Claude Desktop to Claude Code to Cowork
• 25:55 - Skills deep dive: orchestrator, quality gate, flow state
• 39:48 - Research cascade skill demonstration
• 43:18 - Decision panels walkthrough
• 48:58 - 2026 predictions: Ambient AI and pixel-free interfaces

Resources Mentioned:

• Danny's Skills Pack (available to listeners)
• Typora - Markdown editor ($14 lifetime)
• Time Machine backup for Mac users
• Git for version control

Connect with Ritu Java:
LinkedIn

Connect with Danny McMillan:
LinkedIn | Seller Sessions